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Merck
CN

74437

Sigma-Aldrich

(+)-香柏酮

≥99.0% (GC)

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别名:
(4R,4aS,6R)-4,4a,5,6,7,8-六氢-4,4a-二甲基-6-(1-甲基乙烯基)-2(3H)-萘酮
经验公式(希尔记法):
C15H22O
CAS号:
分子量:
218.33
Beilstein:
4676969
EC 号:
MDL编号:
UNSPSC代码:
12352205
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

≥99.0% (GC)

形式

crystals

旋光性

[α]20/D +182.0±5.0°, c = 1% in ethanol

储存条件

under inert gas (Argon)

mp

35-39 °C

储存温度

2-8°C

SMILES字符串

C[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C

InChI

1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1

InChI key

WTOYNNBCKUYIKC-JMSVASOKSA-N

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一般描述

(+)-诺卡酮(Nootkatone)是一种双环共轭倍半萜酮,具有葡萄柚香味,常用于香料、食品、化妆品和医药行业。它可以由(+)-瓦伦烯通过生物转化反应合成。(+)-诺卡酮是香附子(一种著名的中药)抗血小板作用的活性成分。它还具有抗金黄色葡萄球菌生物被膜形成的强效作用。

应用

(+)-诺卡酮可用于:
  • 光照条件下与有机叠氮化物进行铁(III)卟啉催化的烯烃的氮杂环丙烷化反应。
  • 作为底物通过铱催化的还原消除反应合成相应的三烯衍生物。

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Skin Sens. 1

WGK

WGK 2

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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Li J, et al.
Green Chemistry, 21(8), 2088-2094 (2019)
Iron porphyrin catalysed light driven C-H bond amination and alkene aziridination with organic azides
Du Y, et al.
Chemical Science, 11(18), 4680-4686 (2020)
Betty C R Zhu et al.
Pest management science, 66(8), 875-878 (2010-07-06)
Research has shown that the family of grapefruit flavors called nootkatones have significant repellant and toxic effects to Formosan subterranean termites (Coptotermes formosanus Shiraki). Nineteen synthetic nootkatone derivatives, along with three commercially available nootkatone derivatives, were tested for repellent activity
Robert A Jordan et al.
Journal of medical entomology, 49(1), 101-106 (2012-02-09)
We conducted field trials to compare the relative repellent activity of two natural product compounds (nootkatone and carvacrol) with commercially available plant-derived (EcoSMART organic insect repellent) and permethrin-based (Repel Permanone) repellents against adult Ixodes scapularis Say and Amblyomma americanum (L.)
Katarina Cankar et al.
FEBS letters, 585(1), 178-182 (2010-12-01)
Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the

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